New Route of Benzyne Cyclization for Synthesis of 2,3,4,5‐Tetrahydro‐1H‐pyrido[4,3‐b]indole Derivatives Avoiding Highly Toxic Aryl Hydrazines

A new route for the regioselective synthesis of 2,3,4,5‐tetrahydro‐1H‐pyrido4,3‐b]indole derivatives was developed based on cyclization of 3‐chlorophenylimine‐N‐alkyl‐4‐piperidones by “the complex bases” of NaNH₂ or KNH₂. The procedure was performed under variable reaction conditions in inert proton‐free solvents, such as THF, dioxane, 1,2‐dimethoxyethane, toluene, and xylene, at temperatures varying from 20°C to boiling point of the solvent used. Toxic arylhydrazine intermediates occurring in the classical Fischer indole synthesis are avoided.